NO20075095L - Method for Preparation of Salts of 4 - [[5 - [(Cyclopropylamino) carbonyl] -2-Methylphenyl] Amino] -Methyl-N-Propylpyrrolo [2,1-F] [1,2,4] Triazine-6-Carboxamide and new stable variants of these - Google Patents
Method for Preparation of Salts of 4 - [[5 - [(Cyclopropylamino) carbonyl] -2-Methylphenyl] Amino] -Methyl-N-Propylpyrrolo [2,1-F] [1,2,4] Triazine-6-Carboxamide and new stable variants of theseInfo
- Publication number
- NO20075095L NO20075095L NO20075095A NO20075095A NO20075095L NO 20075095 L NO20075095 L NO 20075095L NO 20075095 A NO20075095 A NO 20075095A NO 20075095 A NO20075095 A NO 20075095A NO 20075095 L NO20075095 L NO 20075095L
- Authority
- NO
- Norway
- Prior art keywords
- crystals
- preparation
- methyl
- propylpyrrolo
- cyclopropylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 2
- -1 4 - [[5 - [(Cyclopropylamino) carbonyl] -2-Methylphenyl] Amino] -Methyl-N-Propylpyrrolo [2,1-F] [1,2,4] Triazine-6-Carboxamide Chemical class 0.000 title 1
- 239000013078 crystal Substances 0.000 abstract 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 2
- 235000019253 formic acid Nutrition 0.000 abstract 2
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- GDTQLZHHDRRBEB-UHFFFAOYSA-N 4-[5-(cyclopropylcarbamoyl)-2-methylanilino]-5-methyl-n-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C12=C(C)C(C(=O)NCCC)=CN2N=CN=C1NC(C(=CC=1)C)=CC=1C(=O)NC1CC1 GDTQLZHHDRRBEB-UHFFFAOYSA-N 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229940043355 kinase inhibitor Drugs 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Abstract
Prosesser er gitt for selektiv preparing av nye stabile krystallinske saltformer, selektive og konsistente, dvs. fremstilling av Form N-1 av metansulfonsyresaltet og Form N-1 og Form N-4 av saltsyresaltet av p38 kinase-inhibitoren 4-[[5-[(cyklopropylamino)karbonyl]-2-metylfenyl]amino]-5-metyl-N-propylpyrrolo[2,1-f][1,2,4]triazin-6-karboksamid. Prosessene anvender fortrinnsvis løsningsmiddelsystemer omfattende maursyre/aceton og maursyre/metyletylketon som produserer krystaller som har egnete flytegenskaper og ønsket partikkelstørrelse, og løsningsmidler så som N,N-dimetylformamid og N,N-dimetylacetamid kan også anvendes. Nye Form N-1 krystaller av Form N-1 og Form N-4 krystaller av hydrokloridsaltet og Form N-1 krystaller av metansulfonsyresaltet av den frie basen ovenfor, farmasøytiske preparater inneholdende nye slike former og en metode for behandling av p38 kinaseassosierte lidelser, omfattende revmatoid artritt er også gitt.Processes are provided for selective preparation of novel stable crystalline salt forms, selective and consistent, i.e., preparation of Form N-1 of the methanesulfonic acid salt and Form N-1 and Form N-4 of the hydrochloric acid salt of the p38 kinase inhibitor 4 - [[5- [ (cyclopropylamino) carbonyl] -2-methylphenyl] amino] -5-methyl-N-propylpyrrolo [2,1-f] [1,2,4] triazine-6-carboxamide. The processes preferably employ solvent systems comprising formic acid / acetone and formic acid / methyl ethyl ketone which produce crystals having suitable flow properties and desired particle size, and solvents such as N, N-dimethylformamide and N, N-dimethylacetamide may also be used. New Form N-1 crystals of Form N-1 and Form N-4 crystals of the hydrochloride salt and Form N-1 crystals of the above free base methanesulfonic acid salt, pharmaceutical compositions containing novel such forms and a method of treating p38 kinase associated disorders, comprising Rheumatoid arthritis is also given.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67225505P | 2005-04-18 | 2005-04-18 | |
| PCT/US2006/014504 WO2006113682A1 (en) | 2005-04-18 | 2006-04-18 | Process for preparing salts of 4-[[5-[(cyclopropylamino)carbonyl]-2-methylphenyl]amino]-5-methyl-n-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide and novel stable forms produced therein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO20075095L true NO20075095L (en) | 2007-11-15 |
Family
ID=36693144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20075095A NO20075095L (en) | 2005-04-18 | 2007-10-09 | Method for Preparation of Salts of 4 - [[5 - [(Cyclopropylamino) carbonyl] -2-Methylphenyl] Amino] -Methyl-N-Propylpyrrolo [2,1-F] [1,2,4] Triazine-6-Carboxamide and new stable variants of these |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US20060235020A1 (en) |
| EP (1) | EP1874778B1 (en) |
| JP (1) | JP5047160B2 (en) |
| CN (1) | CN101198610B (en) |
| AR (1) | AR053586A1 (en) |
| AT (1) | ATE452894T1 (en) |
| DE (1) | DE602006011295D1 (en) |
| ES (1) | ES2336363T3 (en) |
| NO (1) | NO20075095L (en) |
| PE (1) | PE20061429A1 (en) |
| TW (1) | TW200716126A (en) |
| WO (1) | WO2006113682A1 (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235551B2 (en) | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
| HRP20040988A2 (en) * | 2002-04-23 | 2005-06-30 | Bristol-Myers Squibb Company A Delaware (Usa) Corp | Pyrrolo-triazine aniline compounds useful as kinas |
| JP2011503232A (en) | 2007-11-20 | 2011-01-27 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッド | Modulating the immune response |
| TW201035100A (en) | 2008-12-19 | 2010-10-01 | Cephalon Inc | Pyrrolotriazines as ALK and JAK2 inhibitors |
| CN103153352B (en) * | 2010-08-18 | 2015-07-15 | 爱默蕾大学 | Compounds and compositions for ossification and methods related thereto |
| WO2012031057A1 (en) | 2010-09-01 | 2012-03-08 | Bristol-Myers Squibb Company | Bms- 582949 for the treatment of resistant rheumatic disease |
| CN104003990B (en) * | 2013-02-21 | 2017-09-15 | 江苏先声药业有限公司 | Heterocyclic amine Hedgehog signal pathway inhibitors |
| WO2015112048A1 (en) * | 2014-01-24 | 2015-07-30 | Huawei Technologies Co., Ltd. | Method and device for cross-polarization interference suppression |
| US20180071376A1 (en) | 2015-03-23 | 2018-03-15 | The Brigham And Women`S Hospital, Inc. | Tolerogenic nanoparticles for treating diabetes mellitus |
| GB2533833B (en) * | 2015-06-22 | 2016-12-14 | Univ Bristol | Wireless ultrasound sensor with two induction coils |
| CN105651804B (en) * | 2016-03-11 | 2017-05-17 | 山西大学 | Evaluating method of chronic atrophic gastritis rat model |
| PT3691620T (en) | 2017-10-05 | 2022-10-06 | Fulcrum Therapeutics Inc | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| WO2020209868A1 (en) * | 2019-04-12 | 2020-10-15 | Bruker Axs, Inc. | A system and method for diffraction-based structure determination with simultaneous processing modules |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200750A (en) * | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
| US5658903A (en) * | 1995-06-07 | 1997-08-19 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
| US5977103A (en) * | 1996-01-11 | 1999-11-02 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| US6147080A (en) * | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| US5945418A (en) * | 1996-12-18 | 1999-08-31 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| US6087496A (en) * | 1998-05-22 | 2000-07-11 | G. D. Searle & Co. | Substituted pyrazoles suitable as p38 kinase inhibitors |
| RU2249591C2 (en) * | 1997-05-22 | 2005-04-10 | Дж.Д. Серл Энд Ко. | 3-(5)-heteroaryl-substituted pyrazoles as kinase p38 inhibitors |
| US6251914B1 (en) * | 1997-07-02 | 2001-06-26 | Smithkline Beecham Corporation | Cycloalkyl substituted imidazoles |
| US6130235A (en) * | 1998-05-22 | 2000-10-10 | Scios Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6184226B1 (en) * | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| HRP20040988A2 (en) * | 2002-04-23 | 2005-06-30 | Bristol-Myers Squibb Company A Delaware (Usa) Corp | Pyrrolo-triazine aniline compounds useful as kinas |
| MY145634A (en) * | 2003-12-29 | 2012-03-15 | Bristol Myers Squibb Co | Pyrrolotriazine compounds as kinase inhibitors |
-
2006
- 2006-04-04 US US11/398,102 patent/US20060235020A1/en not_active Abandoned
- 2006-04-17 AR ARP060101516A patent/AR053586A1/en not_active Application Discontinuation
- 2006-04-18 ES ES06758390T patent/ES2336363T3/en active Active
- 2006-04-18 DE DE602006011295T patent/DE602006011295D1/en active Active
- 2006-04-18 EP EP06758390A patent/EP1874778B1/en active Active
- 2006-04-18 CN CN2006800219258A patent/CN101198610B/en not_active Expired - Fee Related
- 2006-04-18 AT AT06758390T patent/ATE452894T1/en not_active IP Right Cessation
- 2006-04-18 JP JP2008507792A patent/JP5047160B2/en not_active Expired - Fee Related
- 2006-04-18 PE PE2006000402A patent/PE20061429A1/en not_active Application Discontinuation
- 2006-04-18 TW TW095113812A patent/TW200716126A/en unknown
- 2006-04-18 WO PCT/US2006/014504 patent/WO2006113682A1/en not_active Ceased
-
2007
- 2007-10-09 NO NO20075095A patent/NO20075095L/en not_active Application Discontinuation
-
2009
- 2009-06-04 US US12/478,210 patent/US20090312331A1/en not_active Abandoned
-
2011
- 2011-11-10 US US13/293,204 patent/US20120108594A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20120108594A1 (en) | 2012-05-03 |
| AR053586A1 (en) | 2007-05-09 |
| EP1874778B1 (en) | 2009-12-23 |
| EP1874778A1 (en) | 2008-01-09 |
| PE20061429A1 (en) | 2006-12-17 |
| WO2006113682A1 (en) | 2006-10-26 |
| ES2336363T3 (en) | 2010-04-12 |
| ATE452894T1 (en) | 2010-01-15 |
| US20090312331A1 (en) | 2009-12-17 |
| DE602006011295D1 (en) | 2010-02-04 |
| CN101198610A (en) | 2008-06-11 |
| TW200716126A (en) | 2007-05-01 |
| CN101198610B (en) | 2012-06-13 |
| US20060235020A1 (en) | 2006-10-19 |
| JP5047160B2 (en) | 2012-10-10 |
| JP2008538373A (en) | 2008-10-23 |
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